Methyl iodide → HCID 15380284, compound

HRID 743875Notes

Reaction equation

HRID 743875 reaction equation
CC1(C)C[O:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18]([CH:22]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[C:23]([O:25]CC)=[O:24])[CH:17]=[CH:16]3)=N1.CI.C1C[O:40]CC1>>[C:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[N:18]([CH:22]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[C:23]([OH:25])=[O:24])[CH:17]=[CH:16]2)([OH:5])=[O:40]

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 15380283HCID 15380283, compound

Product 1

HCID 15380284HCID 15380284, compound

Procedure

Ethyl 2-[5-[2-(4,4-dimethyloxazolin-2-yl)phenyl]indole-1-yl]octanoate (0.174 mmoles, 80 mg) was dissolved in 1 ml THF. Methyl iodide (0.15 ml, 1.1 mmole) was added. After stirring overnight at room temperature, the solution was concentrated. The residue was dissolved in 7 ml of 2:1 MeOH:2N NaOH and heated at 90° C. for 24 hours. The reaction was cooled to 0° C. and washed with ether. The pH was adjusted to 1.0 using 2N HCL. The product was extracted with 20% EtOH in ethyl acetate. The organic layer dried and concentrated to yield 35 mg of 2-[5-(2-Carboxyphenyl)indol-1-yl]octanoic acid that solidified upon standing. (MS)

Workup

  1. concentrationthe solution was concentrated
  2. dissolutionThe residue was dissolved in 7 ml of 2:1 MeOH
  3. temperature2N NaOH and heated at 90° C. for 24 hours
  4. temperatureThe reaction was cooled to 0° C.
  5. washwashed with ether
  6. extractionThe product was extracted with 20% EtOH in ethyl acetate
  7. customThe organic layer dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d273e443d8f64c159732d9ee5b326a4e
Source dataset
uspto-grants-1996_09
Patent number
US05556981

Reaction notes

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